If you can go anywhere, consider the Chesapeake - fairly long season, lots of interesting nooks and crannies to explore, small tides, and soft bottom if you run aground. Downsides: light winds in summer, expensive.

 

As long as you stay in your boat, you can't get hurt, but definitely get towing assist. as you will run aground in soft mud.
Dick

 

Wow, how many novice sailors get to choose their cruising waters...how lucky is that? However, if you are looking continental US, I agree with Wing'n'wing - Chesapeake looks like a winner. So Cal might be nice too , but I have never sailed there. Picking a sailing area is like a box of chocolates...

 

Actually, the best sailing ground to learn in is the one you can get to often.

Stay home, learn to sail, then go exploring.

I see on your other thread that you are a power boater moving to sail. While your season is short where you are it's enough to learn. Save the travel time and take some courses/charter a boat locally, then start to look to distant horizons.

 

Chuck has a good point, what ever gets you on the water the most is a great place to start.
If that is Lake Michigan, Lake Michigan is a great body of water to sail on, it is wide open with very few obstructions. This I consider a good thing for learning.
However, you have to be careful of a few things; It is very congested with heavy boat traffic around the major cities such as Chicago and Milwaukee. This also can be a good thing for learning because you are constantly on the look out for other pleasure boaters along with very large commercial craft and sight seeing boats.
The other thing as you know is it can get brutally rough in the right / wrong conditions AND it changes as fast as you can say reef. Again, this is both good and bad as the learning curve is quick as well. You will quickly learn that you don't want to be out on Lake Michigan when it is blowing 30 out of the North. .
If you have access now to Lake Michigan, it is a fine place to sail, the season can be stretched to about 6 months. Other than a short season, it has a lot to offer.

 

Hmmmm??

Anywhere there's enuff water under the keel to float and space enuff to tack once or twice

Like the others have already said... go close; go often! WHile I believe I'd like to sail in the warm weather of the Keys; I'm settling for the N. Chessie 'cause it's only an hour away. Helluva commute to Florida!

 

If money/convenience were no object, I'd have to say anywhere the other guys are suggesting that affords year-round sailing in temperate waters with a good variety of wind conditions. Otherwise, they are spot on- hook up with a local club and learn to sail in a dinghy. We just had around 35 boats (J22's, FJ's and 420's) in a first-off regatta in Charleston and yesterday people were sailing in t-shirts and shorts.. pretty hard to beat! I would suggest it all depends on what you want and how much you can afford.

 

What about the Keys? Is that friendly water for a beginner this time of year?

 

There is a saying; "If you can sail the Bay, you can sail ANYWHERE on earth."
San Francisco Bay has the most varied sailing conditions of any place I have ever sailed. In a half day you can sail light air to gale force winds and back, through fog or currents that can turn a 65' staysail schooner under full sail in 30 knots of wind, 180 degrees, leaving you with all sails back-winded and your spreaders in the water.
In over 50 years of sailing, I have never sailed in more challenging and varied conditions in one place.

 

The conditions you describe are not the best for a beginner..... But yes San Francisco bay does offer alot, I was just out there this summer, but it is only a fraction of the size chesapeake. Sailing New England would be a great spot too, but the season is fairly short.
I would say pick the weather and living conditions you require and move your sailing there. Here on the Ches...it hot and humid. SF bay is cool and lots of wind but cost of living is a bit much and very populated,.......

 

Close to home so you can use the boat as often as possible

 

I don't think I would suggest the Keys for beginner sailing. Especially if you are singlehanding. I just went on a singlehanding down there this past year and it was fun but it was pretty darn challenging.

-Two tides a day so you swing on your anchor a good bit at night
-Good bit of places to run aground
-Not a good place to be in hurricane season (especially if your a few days from your vehicle)
-It a little intimidating overall

Now if I hadn't been alone I think it would have been alot more laid back and I wouldn't have been so stressed.

Also, it depends on what size boat your on to. I was on my Montgomery 17.

 

If I may...

The west coast of Florida is, in my opinion, a perfect place to learn to sail. From Tampa Bay south to Fort Myers or so, specifically. You can start out in small dinghies in the smaller bays, sounds and inlets, where it's shallow, but there is much to explore. You can graduate into the bigger bays (Tampa Bay, Charlotte Harbor), and bigger boats if you like. You can explore up and down the coast via the Intracoastal Waterway, and stay in protected waters the entire time. When you're ready, you can venture out into the Gulf - and from there, as you know, you can go anywhere in the world that water can take you

--arthur

 

Thanks for the feedback. Yes, Lake Michigan can get brutal. I'll try to put up a pic and vid of how fast it turned and caught some people in just a day right after July 4th. I was getting smack from family on why I didn't bring the 20' Bayliner up there for a family reunion. The pic and vid will show why, as I'm a cautious guy.

 

Partial to Florida... I'd pick beautiful waters with plentiful beaches to take a break on...

 

Lake Michigan, I sail first of April till first second week November. Then you can trailer sail a smaller boat before and after those dates until freeze-up which is not very long anymore. Grand Rapids area has cheap living and easy access to boats. Crew on bigger boats daysail your own small boat.

 

As was said by a few prior the closer to home the better. We started on a small man made lake less then an hour from our house (good when you forget to bring your sails back to the boat). It made the 1st mate comfortable knowing if something went wrong she could swim to shore. Being our 1st boat was a C-21 there was enough room to enjoy the 13 weekends we spent learning to sail and that it was more then something then a hobby.

The east coast waters have been great for sailing but we learned quick that things can go wrong and was very happy that we learned how to handle things first on the lake.

 

Without knowing more details from OP's objective, I would say Chesapeake Bay would be a good place to start for mere learning and practice sailing skills. Plenty of sailing at the bay and countless sailing clubs and with many good sailing school that meet various budget.

One characteristic that Chesapeake wins over other sailing areas in the States is its late afternoon summer storm. It is the best preparation if one thinking about going off shore in the future. The storm will come fast and be gone in 15 to 20 minutes. When you think your are going to die and a moment later, it is blue sky. When you driving home, you can review in your head what you had done right and what you need to prepare more. Think about how the boat reacted in the storm, think about the HS physics he learned about vector and moment acted on the CG, read more books, talk to other captains for their advices, and repeat this again until it becomes your second nature. I found this is the quickest way to learn to be self reliant, if this is what you are seeking.

At the beginning, make sure you have lot of sea room or bring on another sailor to help you in case you need help. Once everything hunker down properly, the sailboat will take care her own. I just stand on the companion way to enjoy the storm to pass.

This is not for everyone obviously, My wife hates it. But this is the best what Chesapeake has to offer to prepare the sailors before going to the big Pond. The problem in the Big Pond is that the storm lasts for days. It sucks when you don't know if you ever will see you family again.

As always, YMMV

 

I'll give another vote to the west coast of FL. We sail year round out of St. Petersburg. There are active sailing communities from Clearwater down to Naples.

We've been making two and three day trips from Tampa Bay down to Charlotte Harbor the last couple years and made one offshore trip to the dry tortugas. Once you get bored of that you can head to Mexico, the Bahamas or just get drunk in Key West for a while.

 

From a beginner: I started in 2010 with ASA 101, 103 & 104 lessons in Santa Barbara within an 8-day period. Slept on the boat; sailed during the day. Terrific experience! During the 2011 season we time-shared a sailboat out of Belmont Harbor in Chicago. Another great experience - but everything said above about the perils of Lake Michigan is true. We learned a lot! Last January we rented a cottage for a week in the Florida Keys that came with a 23' Com-Pac. We sailed most every day on the bay side. Great time! This past June we spent two weeks in the San Juan Islands; first week was with an instructor so my spouse could complete ASA 101, 103 & 104; second week it was just the two of us hopping from harbor to anchorage. Fantastic!

What I am saying is that it is hard to go wrong - every experience we have had has been challenging and immensely satisfying. Plus, I think we have gained by sailing in different waters.

But if I were to pick one of these spots, it would be the San Juans. The land masses of the Islands buffer the winds and wave heights of the Pacific, so it is rare to have to manage anything over 15 knots (though I do remember being out on the deck reefing the main in 24+ knots). The scenery is spectacular. You can alternate between harbors one night (with showers) and anchorages/moorings the next. As a beginner, you'll learn currents and tides in ways you won't on Lake Michigan; every day is a different docking or mooring/anchoring experience, and that's good experience.

Enjoy!

 

From a beginner:

But if I were to pick one of these spots, it would be the San Juans. The land masses of the Islands buffer the winds and wave heights of the Pacific, so it is rare to have to manage anything over 15 knots (though I do remember being out on the deck reefing the main in 24+ knots). The scenery is spectacular. You can alternate between harbors one night (with showers) and anchorages/moorings the next. As a beginner, you'll learn currents and tides in ways you won't on Lake Michigan; every day is a different docking or mooring/anchoring experience, and that's good experience.

Enjoy!

The tidal current in the SJ's is serious business. I am not sure that would be the best for a beginners training ground. You need to be spot on with the charts also as there are numerous areas with rock outcroppings. No such thing as a "soft grounding" in the SJ's, very hard around the edges. The winds are also very inconsistent in the summer. Even though I am from Puget Sound area I might cast my vote for west coast Florida as good training ground if the OP is serious about re-locating for learning. Otherwise, I would stay in OP's local cruising area for sailing and do it often.

But man o' man it is beautiful up in the San Juans, can't wait 'till summer gets here and head up. When I was over in the NE, I was amazed how similar Penobscot Bay was to the San Juan's. Albeit, Penobscot was much more crowded.

 

Southern California is pretty gentle and there are lots of destinations but it's expensive and there are lots of rules and lots of law enforcement. The Banderas Bay around Puerto Vallata is really consistent and again lots of destinations, anywhere from 5 miles to hundreds of miles and it's a LOT cheaper and a lot warmer than California.